Chatham Rentals
From $404 per night (USD)VRBO
Chatham Beach Cottage + loft Walk to the Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Relax with the whole family at this year round Charming Chatham Seaside Cottage , with just a short 5 minute walk to a b ...
From $404 per night (USD)VRBO
From $1727 per night (USD)Expedia
Royal Retreat: 935-C Renovated Luxury Chatham Home with Pool & Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This property is professionally managed by Pretty Picky Properties Renovated Luxury Chatham Home with Pool & Hot Tub Ho ...
From $1727 per night (USD)Expedia
From $548 per night (USD)VRBO
Centrally located home with patio, a/c included, walking distance from town.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Centrally located vacation home with central air conditioning in an ideal location with 3 bedrooms, 2 full baths plus ...
From $548 per night (USD)VRBO
From $968 per night (USD)VRBO
FIVE BEDROOM -- AMAZING WATER VIEWS OF NANTUCKET SOUND, MINUTES TO ASSOCIATION BEACH
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 11
Just 1/10 of a Mile to Deeded Association Beach with amazing water views of Nantucket Sound. * * * * See end of ...
From $968 per night (USD)VRBO
From $282 per night (USD)VRBO
Wrap-Around Porch Mins. to Beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: 16643 - Tidal Treasure: Wrap-Around Porch Mins. to Beach! The Space: There isn’t a much more beautiful place t ...
From $282 per night (USD)VRBO
From $948 per night (USD)Expedia
Luxurious Waterfront Home!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
Summary: 15526 - Nautical Dream: Luxurious Waterfront Home! The Space: Orleans, Cape Cod is a picturesque town full of ...
From $948 per night (USD)Expedia
From $486 per night (USD)VRBO
Three Bedroom Updated Home -- Just Minutes to Pleasant Bay, Town and Bike Path!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sun Filled, Completely Renovated 3 Bedroom, 2 Bath. Minutes from Pleasant Bay or Downtown, Perfect for your Cape Adven ...
From $486 per night (USD)VRBO
From $899 per night (USD)VRBO
Charming 3 bedroom 2.5 bath sleeps 6 - Walk to Town & Oyster Pond
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
A charming 3 bedroom, 2.5 bath cape with large kitchen and private backyard, patio and deck that abuts conservation lan ...
From $899 per night (USD)VRBO
From $386 per night (USD)VRBO
New construction home on quiet, private waterview lot near Pleasant Bay
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
We will provide an additional $250 discount for singles or couples -- please send a message and we'll discuss how to imp ...
From $386 per night (USD)VRBO
From $550 per night (USD)Expedia
The Boarding House, King bed comfort. Close to Nantucket Sound beaches.
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
This completely renovated 4 bedroom cape is less than 3 miles from Nantucket Sound beaches. Inside there is central air ...
From $550 per night (USD)Expedia
From $356 per night (USD)VRBO
1 Mi to Town & Oyster Pond Beach: Chatham Retreat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Recently built and only 1 mile from Oyster Pond Beach, this Chatham vacation rental has everything you need for your nex ...
From $356 per night (USD)VRBO
From $315 per night (USD)Expedia
Chatham Seaside Cottage - Oceanfront Beach Cottage - Spectacular Views
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
On over two acres of Oceanfront, 'Bayberry and Seadaisy Cottages at Ridgevale Beach face the temperate waters of Nantuc ...
From $315 per night (USD)Expedia
From $1136 per night (USD)VRBO
Gorgeous Luxury Waterfront Retreat: Pool, Tennis, Pickleball, Kayaks
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
This picture perfect Townhome is set on 17.5 acres on beautiful Oyster. Beautifully and meticulously designed, this Town ...
From $1136 per night (USD)VRBO
From $874 per night (USD)Expedia
Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Ocean Harbor Waterfront. Stunning downtown Chatham Waterfront location with panoramic views, (Little Mill Pond) with ...
From $874 per night (USD)Expedia
From $416 per night (USD)VRBO
5BR-Beautiful Chatham-Year Round-Sleeps up to ten (10) & 1 Mile to Town!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
My family and i live full time in lexington, ma. We decided to purchase a vacation home in chatham, ma because of the sh ...
From $416 per night (USD)VRBO
From $567 per night (USD)Expedia
Walk to Beach-Water views-Central A/C and WiFi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
3 Bedroom- 2 Bathroom- Sleeps 8 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $567 per night (USD)Expedia
From $477 per night (USD)VRBO
Pleasant Chatham Cape
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Pleasant Chatham Cape - A Classic Cape Cod Getaway with Modern Comforts Welcome to Pleasant Chatham Cape, a charming 4- ...
From $477 per night (USD)VRBO
From $1594 per night (USD)Expedia
Fabulous Family CapeHouse, with Views, Beach and Dock!
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 14
This sprawling family beach home is perfectly located on a hilltop with 3.5 acres overlooking Pleasant Bay in South Or ...
From $1594 per night (USD)Expedia
From $488 per night (USD)VRBO
Solitude near the beach, High speed wifi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Comfort, convenience and beauty a mere 5 minute stroll away from Ridgevale beach. Nestled in a quiet neighborhood, our b ...
From $488 per night (USD)VRBO
From $858 per night (USD)Expedia
Spacious Home on the Loop in Chatham
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Located on the Loop in scenic Chatham, this house rents Sunday to Sunday. The large living room opens onto a deck with ...
From $858 per night (USD)Expedia
From $348 per night (USD)VRBO
~ 4 Mi to Dtwn: Chatham Home w/ Fire Pit
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
1,802 Sq Ft | Furnished Deck w/ Gas Grill | Fireplace | 13 Mi to Whydah Pirate Museum Welcome to the good life! Whether ...
From $348 per night (USD)VRBO
From $2645 per night (USD)VRBO
Location! Pool & Spa! 2 Primary Suites, Walk to Town, Beach, Chatham Bars Inn
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
**As is customary with Cape rentals, there is a cleaning fee and a 14.45% local and state lodging tax. Please enter desi ...
From $2645 per night (USD)VRBO
From $1238 per night (USD)VRBO
Charming and updated home with private gardens and patio!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Discover a charming and updated vacation rental that comfortably sleeps eight, ideally situated on "The Loop." This home ...
From $1238 per night (USD)VRBO
From $1451 per night (USD)Expedia
Luxury 4 Bedroom Harwich Home - Centrally Located
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Our home is located close to East Harwich shopping centers, restaurants, and Pleasant Bay for boating, fishing, and swim ...
From $1451 per night (USD)Expedia
From $583 per night (USD)VRBO
Serene home with WiFi, deck, & outdoor fireplace - walk to beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Harwich Tranquility Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $583 per night (USD)VRBO
Click For PricingExpedia
Large Yard, Quiet; 300 Yd on Sidewalk to Hardings Beach
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
If you have small children or would just like some peace and serenity, Blue Skye is for you. Lots of lawn to run and pl ...
Click For PricingExpedia
From $442 per night (USD)VRBO
Full Renovation! Amazing Spot with Views!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: 16620 - A Step Above: Full Renovation! Amazing Spot with Views! The Space: Our completely renovated and newly ...
From $442 per night (USD)VRBO
From $115 per night (USD)VRBO
Pleasant Forest Shores #1 S. Chatham: Classic Swedish ''Stuga'' style near beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
NOTE: Booking of EXISTING customers should begin on 02/01/25. New guests can ONLY apply for 2025 WAIT LIST at this time ...
From $115 per night (USD)VRBO
From $681 per night (USD)VRBO
Pet friendly and spacious home in quiet neighborhood!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Spacious three bedroom, two and half bath home in Riverbay offers plenty of living space on a 1/2 acre wooded corner lot ...
From $681 per night (USD)VRBO
From $404 per night (USD)Expedia
Beautiful Home w/ Artistic Flair!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Summary: 16657 - Artist's Haven: Beautiful Home w/ Artistic Flair! The Space: On the Cul-de-sac of a private Chatham ne ...
From $404 per night (USD)Expedia
From $674 per night (USD)VRBO
Centrally Located Home w/ Patio Fire Pit!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Summary: 16658 - Home Base: Centrally Located Home w/ Patio Fire Pit! The Space: Conveniently situated in the middle of ...
From $674 per night (USD)VRBO
From $463 per night (USD)Expedia
North Chatham, Quaint Cottage, Great Yard, Welcome to Bobs Place
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
2 Bedroom - 1 Bathroom - Sleeps 4 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Ma ...
From $463 per night (USD)Expedia
Click For PricingVRBO
Vacation in downtown Chatham close to Lighthouse Beach
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 11
Spend your Cape Cod vacation in this rental perfectly situated in the heart of downtown Chatham. We're just a half-mile ...
Click For PricingVRBO
From $304 per night (USD)VRBO
Quaint 2 Bedroom Cottage Overlooking White Pond
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Must bring your own linens. Perfect getaway to relax and unwind. Located in a small 5 acre enclave of cottages nestled u ...
From $304 per night (USD)VRBO
From $1163 per night (USD)VRBO
Location and Luxury
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
LOCATION: The cottage is located in Chatham's old village, just a block from the ocean. The closest beach is Andrew Har ...
From $1163 per night (USD)VRBO
From $1106 per night (USD)VRBO
Family friendly luxury home with heated pool and spa
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Gorgeous home in Chatham with a brand new heated saltwater pool and hot tub. The open floor plan, combined living and ...
From $1106 per night (USD)VRBO
From $299 per night (USD)VRBO
Cozy one bedroom on White pond (Must bring your own linens)
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
2 Person only. Charming little classic Cape cottage located close to town, beaches and bike trail. The cottage is nestl ...
From $299 per night (USD)VRBO
From $778 per night (USD)Expedia
Refreshed Interior Central AC WIFI Large Yard Deck Great Chatham Location
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
4 Bedroom - 2 Baths - Sleeps 10 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $778 per night (USD)Expedia
From $314 per night (USD)VRBO
Classic home with deck, patio & yard - walk to Cockle Cove & Forest Beaches
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
South Chatham Sunshine Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $314 per night (USD)VRBO
From $1001 per night (USD)Expedia
Reuben Young House: Two 1st Floor King Master Suites. Close to Town & Beaches.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Charming circa 1820 antique newly renovated. close to downtown Chatham (1.5 miles). Close to Fish Pier, Ryders Cove, Oys ...
From $1001 per night (USD)Expedia
From $515 per night (USD)VRBO
Chatham walk to Cape Cod beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
A Very Short Walk to Hardings Beach. Ocean-side private neighborhood. Chosen by Condé Nast Traveler as “One of the Bes ...
From $515 per night (USD)VRBO
From $271 per night (USD)Expedia
Charming Downtown Chatham
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Charming in town apartment above retail shops overlooks the Main St. Walk to beaches, nearby shops & restaurants, band c ...
From $271 per night (USD)Expedia
From $307 per night (USD)VRBO
Chatham 3 Bedroom/2 Bath Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautifully renovated and spacious 3 Bedroom 2 Full Bath Home on a private 1/2 acre setting in one of Chatham's sought a ...
From $307 per night (USD)VRBO
From $372 per night (USD)VRBO
Lovely Stage Harbor Estate Guest House W/Private Beach to Use
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Lovely guest house on quiet and picturesque Stage Harbor! Right on town way with 30 second walk to the water and use of ...
From $372 per night (USD)VRBO
From $782 per night (USD)VRBO
Near beach and town, private, AC, pet friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
3 Bedrooms- 3 Bathrooms- Sleeps 8 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Ma ...
From $782 per night (USD)VRBO
From $606 per night (USD)Expedia
Stunning 3BR Home - Close to Town & Beaches (2159)
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Nestled in East Harwich, this beautiful 3BR/3BA Harwich home features a welcoming open floor plan with high ceilings, ha ...
From $606 per night (USD)Expedia
From $551 per night (USD)VRBO
Excellent Chatham Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This Chatham beauty is a Newly built cottage which is walking distance to Pleasant Bay and a short drive to town. A per ...
From $551 per night (USD)VRBO
From $867 per night (USD)Expedia
From $984 per night (USD)VRBO
Charming two year old 3Bd Rm 4 bath home .6mi to Ridgevale Beach
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Newly built home, app 2900 sq feet, The 1st floor includes a master bedroom with private bath with tub/shower, king siz ...
From $984 per night (USD)VRBO
From $372 per night (USD)Expedia
Chatham! 3BR house, large quiet yard, 5 min to beach, walk to shops, restaurants
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Cape Cod style home with a large, private yard, sunny deck, outdoor shower and hammock in a quiet Chatham neighborhood. ...
From $372 per night (USD)Expedia
From $866 per night (USD)VRBO
Gorgeous Luxury Waterfront Retreat: Pool, Tennis, Pickleball, Kayaks
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 8
This picture perfect Townhome is set on 17.5 acres on beautiful Oyster Pond in the heart of Chatham, Cape Cod, Massachus ...
From $866 per night (USD)VRBO
From $784 per night (USD)VRBO
WATER VIEW OF STETSON COVE! UPDATED HOME WITH SO MUCH TO OFFER!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Sparkling Updated Home With Lovely Views Of Stetson Cove * * * * See end of this description for information a ...
From $784 per night (USD)VRBO
From $6793 per night (USD)VRBO
Your Ultimate Vacation Destination!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
This is your ultimate vacation destination! Simply stunning, custom built home with a grand farmer's porch! Sit and sip ...
From $6793 per night (USD)VRBO
From $594 per night (USD)VRBO
Happy Yellow House - Family and pet-friendly; walkable to Ridgevale Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
*Note: The minimum stay dropped to 3 nights for Jan-March! Other months are still 7 nights as a minimum. The monthly dis ...
From $594 per night (USD)VRBO
From $637 per night (USD)VRBO
CHATHAM WATER FRONT/VIEW HOUSE FIRST TIME RENTAL
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Perfect vacation spot. Enjoy your vacation on this 3 bedroom 2 bath, Central air conditioned house bordering Emery Lake ...
From $637 per night (USD)VRBO
From $613 per night (USD)Expedia
Air Conditioned, King bed Comfort .Dog friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Cranberry Cove, beautiful bright open-plan 3 bedroom house with central AC, a great room made for family time, with vaul ...
From $613 per night (USD)Expedia
From $282 per night (USD)VRBO
Cozy Cottage close to Beaches, Boating, Biking, Shopping and more
- Bedrooms:
- 0
- Bathrooms:
- 2
- Sleeps:
- 5
Centraly located on the elbow of Cape Cod, cozy little cottage in isolated neighborhood of like summer homes. Two bedroo ...
From $282 per night (USD)VRBO
From $497 per night (USD)Expedia
Secluded Chatham Cape Cod House Stage Harbor Area
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Very secluded 3br family friendly (pets considered) full Cape at the end of a cul-de-sac. Located in rural Stage Harbor ...
From $497 per night (USD)Expedia
From $340 per night (USD)VRBO
Fabulous Quiet Cape, Close to Beach, Central Air, Perfect for Families
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Enjoy your quiet family get-away in a lovely, newer construction beautifully decorated cape with central air. Just a co ...
From $340 per night (USD)VRBO
From $644 per night (USD)Expedia
Cozy Cape near Chatham Center
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
You will be sure to enjoy your time in the idyllic town of Chatham, MA in Cape Cod. Our home is 1/2 mile from the qua ...
From $644 per night (USD)Expedia
From $423 per night (USD)VRBO
Lovely Cape Cottage Home < 1 mile to the beach!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Relax at this charming South Chatham coastal retreat! Situated just 0.8 miles to Forest Beach & close proximity to the C ...
From $423 per night (USD)VRBO
From $471 per night (USD)VRBO
Harwich Cape Escape: Minutes from Everything!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Harwich Cape Escape: 4 Bedrooms, 2.5 Baths, Sleeps 8 This beautiful two-story 4BR/2.5 BA Cape Cod home features almost ...
From $471 per night (USD)VRBO
From $408 per night (USD)VRBO
Close to Hardings Beach & Private Access to Oyster River
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Comfy and cozy four bedroom home near Hardings Beach! This recently updated Cape cottage is filled with new furnishings, ...
From $408 per night (USD)VRBO
From $626 per night (USD)VRBO
Stylishly Furnished Home- Access to Pleasant Street Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
*Cancellation policy at end of property description.* Sophisticatedly furnished and well maintained 3BR/2BA with a bon ...
From $626 per night (USD)VRBO
From $673 per night (USD)VRBO
Fantastic Rooftop Deck * 3 Min Walk to Ocean Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
In a Few Words Walk to the beach from this classic New England cottage. Head to the rooftop deck for coffee or cocktai ...
From $673 per night (USD)VRBO
From $704 per night (USD)VRBO
Family Friendly Home with Private Bog View-Close to 2 beaches & town center.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Newly remodeled in 2020, this designer 4 BR, 3 full bath house sleeps 10 (8 preferred) and has everything you need to ma ...
From $704 per night (USD)VRBO
Click For PricingVRBO
Pet friendly! Beautiful decor and great outdoor entertaining space for the whole family.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Enjoy your Chatham vacation at this spacious, newly furnished, 4 bedroom, 3 bath home. Offering 1 king, 2 queens, a bunk ...
Click For PricingVRBO
From $1408 per night (USD)Expedia
Spend your quintessential Cape Cod vacation, in a beautifully renovated 1862 Farm House on Stage Harbor Road!
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 13
Experience your quintessential Cape Cod vacation in a beautifully renovated 1862 Farm House on Stage Harbor Road! Lush g ...
From $1408 per night (USD)Expedia
From $550 per night (USD)VRBO
Amazing Location! Lakefront Waterside Deck
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: 16629 - Dock Holiday: Amazing Location! Lakefront Waterside Deck The Space: Get ready for a week of rafting, c ...
From $550 per night (USD)VRBO
From $544 per night (USD)Expedia
Walk to Chatham Center or bike the Cape Cod Rail Trail!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Wonderful summer rental, filled with new furnishings and centrally located in Chatham! The Cape Cod Rail Trail is right ...
From $544 per night (USD)Expedia
From $374 per night (USD)VRBO
Kid-Friendly Ridgevale Beach is an easy stroll from this comfy beach house!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
.... PET FRIENDLY! ... Recently updated, this classic summer beach cottage is a quick walk to popular Ridgevale Beach! A ...
From $374 per night (USD)VRBO
From $313 per night (USD)VRBO
Luxury Chatham Town Home. Close to town & beaches!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Sunlight filled luxury town home overlooking a beautiful pond, with three floors of living space. Located less than a mi ...
From $313 per night (USD)VRBO
From $488 per night (USD)VRBO
Bright S. Harwich Home, Private Backyard, Close to Beaches, Bike Trail & Shops
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful single family home in South Harwich, conveniently located right off of Rt. 28. Only 500 feet from the Cape Cod ...
From $488 per night (USD)VRBO
From $337 per night (USD)Expedia
15 Minute Walk to Pleasant Street Beach!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: 16632 - Casa Al Mare: 15 Minute Walk to Pleasant Street Beach! The Space: Your perfect seaside getaway starts ...
From $337 per night (USD)Expedia
From $620 per night (USD)VRBO
🐶 Dog Friendly Fenced in Yard! 3/2 🏠 1.1 mi to 🏝 WIFI - perfect fall rental!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Modern 3 bedroom, 2 full bath ranch style home located in Chatham! 1/10th of a mile to Old Colony Bike path and 1.1 mile ...
From $620 per night (USD)VRBO
From $709 per night (USD)VRBO
Perfectly located, with central AC. 3BR, sleeps 6-8
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Our house has undergone a complete renovation with all new updates. The house has a complete master suite on the first ...
From $709 per night (USD)VRBO
From $474 per night (USD)VRBO
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Lucky Number Seven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $474 per night (USD)VRBO
From $272 per night (USD)Expedia
WALK TO RESTAURANTS, SHOPS & LIQUOR STORE! CLOSE TO DOWNTOWN CHATHAM!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This adorable cottage is in an ideal location in West Chatham! Located on a quiet cul-de-sac with five other homes. A 5 ...
From $272 per night (USD)Expedia
From $844 per night (USD)VRBO
Gorgeous panoramic views of Mill Pond and just a short walk to downtown Chatham!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Gorgeous panoramic views of Mill Pond and just a short walk to downtown Chatham! Experience beautiful water views with y ...
From $844 per night (USD)VRBO
From $606 per night (USD)VRBO
1 Mi to Beach: Home w/ Fire Pit & BBQ in Cape Cod!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
2,688 Sq Ft | Dog Friendly w/ Fee | Wet Bar | Expansive Yard Nestled in the heart of South Chatham, this 3-bed, 2.5-bat ...
From $606 per night (USD)VRBO
From $736 per night (USD)VRBO
Walk to town, baseball games, Oyster Pond
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
This well-maintained and updated 4 bedroom, 2 bath home is an excellent choice for your Chatham vacation. With two quee ...
From $736 per night (USD)VRBO
From $592 per night (USD)Expedia
Sleeps 10+/Walk To Buck's Pond Lake! Close To Beach/Golf/Restaurants
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
You will never have to get in your car after arriving. Relax on the deck. Walk with the kids to Buck's Pond. We have ...
From $592 per night (USD)Expedia
From $819 per night (USD)VRBO
Water View-Walk town/beach, pets considered, Linen Option
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
It's all about LOCATION-just steps from deeded access to the Mill Pond where you can launch your Kayak without ever havi ...
From $819 per night (USD)VRBO
From $802 per night (USD)Expedia
Water Views in Chatham!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
*Cancellation policy at end of property description.* Charming, perfect location and every amenity you could want! Th ...
From $802 per night (USD)Expedia
From $719 per night (USD)VRBO
Located in the heart of downtown Chatham, this gem offers an easy walk to everything.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Located in the heart of downtown Chatham, this gem offers an easy walk to dinner, ice cream, shopping, a movie, Oyster P ...
From $719 per night (USD)VRBO
From $446 per night (USD)Expedia
Waterfront on Private Lake!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Summary: 16644 - Lover's Lookout: Waterfront on Private Lake! The Space: Enjoy your best days of summer at our waterfro ...
From $446 per night (USD)Expedia
From $1888 per night (USD)VRBO
Booking for Summer 2025!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 14
Heated Pool and hot tub! Close to Chatham Bars Inn and downtown Chatham. Perfect location for a small or large family/fr ...
From $1888 per night (USD)VRBO
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Charming home in downtown Chatham
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Main Street in Chatham! Spend your summer vacation relaxing on the front porch of this charming, quintessential Cape Cod ...
Click For PricingExpedia
From $515 per night (USD)VRBO
Cape Cottage - 10 minute walk to Red River Beach
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Classic Cape House just minutes away from Red River Beach! 3 BDR, 1 BA, last house on quiet dead end street. Short wal ...
From $515 per night (USD)VRBO
From $640 per night (USD)Expedia
BEST OF ALL WORLDS! Beach, Lake, Town, Bike, and Comfort.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Vivian's Hideaway! Experience all that Cape Cod has to offer in an amazing indoor and outdoor living space, n ...
From $640 per night (USD)Expedia
From $1553 per night (USD)VRBO
Gracious home 200 yards to private beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
This beautiful Cape Cod "gem" was built as a barn in the 1800s and converted to a home by our grandparent's in the 1950s ...
From $1553 per night (USD)VRBO
From $510 per night (USD)VRBO
Perfect couples escape. Close to beaches, great biking & walking & pet friendly.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This open studio apartment is the perfect stay. Privacy, beach proximity, pet friendly and CLEAN. Lots to do and see in ...
From $510 per night (USD)VRBO
Click For PricingVRBO
Completely renovated 3 bedroom home offering comfort and relaxation.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Immaculate ranch in quiet neighborhood. This completely renovated 3 bedroom home offers comfort and relaxation. Relax on ...
Click For PricingVRBO
From $991 per night (USD)VRBO
Four Bedroom home with Water Views of Saltwater Millpond & Mitchell River -- Close to Town and Oyster Pond Beach.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
3200 Square Foot Cape with Spectacular Water Views of Millpond, the Mitchell River and Stage Harbor in the Distance. * ...
From $991 per night (USD)VRBO
From $371 per night (USD)VRBO
Robin's Nest - Dog Friendly Chatham 4 Bedroom
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
This home is represented by Nauset Rental, a local vacation rental management company. Beautiful, spacious 4 bedroom, 2 ...
From $371 per night (USD)VRBO
From $588 per night (USD)Expedia
Lovers Lake Lookout: 448-C Waterfront Renovated Chatham Home with Dock
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This property is professionally managed by Pretty Picky Properties Waterfront Renovated Chatham Home with Dock Sleeps ...
From $588 per night (USD)Expedia
From $347 per night (USD)VRBO
Pool Table, Bar, Ping Pong, Sun Rm, Deck,4 BR, Private
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
This North Chatham 4 BR home with central AC has plenty of room for families to spread out and enjoy a relaxing Chatham ...
From $347 per night (USD)VRBO
From $289 per night (USD)Expedia
Location, Location, Location!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Comfortable, stylish Cape Cod home close to everything. Beach is .7 miles, Route 6 is 3 miles, Downtown is 1.5miles, Bik ...
From $289 per night (USD)Expedia
From $310 per night (USD)VRBO
Beautiful Downtown Chatham 1 Bed, Close to the Beach - Newly renovated + Patio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This gorgeous home is the perfect getaway for those who want to be near downtown Chatham & the beach. Walk to shops, res ...
From $310 per night (USD)VRBO
From $358 per night (USD)VRBO
Modern, RENOVATED, 3-bed PeachTree House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Chatham's Peach Tree Cottage is NEWLY RENOVATED and minutes from the beach on a quiet residential cul-de-sac surrounded ...
From $358 per night (USD)VRBO